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Orphan Annie's Schoolhouse Inn

8097 School St., Baileys Harbor, WI
Orphan Annie's Schoolhouse Inn
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18 reviews from our community

Traveler rating
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Rating summary
  • Sleep Quality
    4.5 of 5 stars
  • Location
    4.5 of 5 stars
  • Rooms
    5 of 5 stars
  • Service
    4 of 5 stars
  • Value
    4 of 5 stars
  • Cleanliness
    5 of 5 stars
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Chicago, Illinois
Senior Reviewer
6 reviews 6 reviews
6 hotel reviews
4 helpful votes 4 helpful votes
5 of 5 stars Reviewed September 5, 2014

I really enjoyed my stay here. It is a converted schoolhouse which has 5 suites; we stayed in the Light House suite. Loren and Annie were very welcoming and great hosts. Check in was smooth; I was on a bike and they let me park it in the shed. The room itself was spacious, clean and quiet. It's basically one... More 

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kiel
2 reviews
5 of 5 stars Reviewed August 6, 2014

This place was wonderful. Loren and Annie did a great job decorating, and were very friendly. They genuinely cared about if we were having a good time. Upon arrival they gave us quite a bit of reading material that highlighted the attractions of the area. They were very approachable the entire time. We will be staying here again; perhaps next... More 

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Halstead, Kansas
Top Contributor
206 reviews 206 reviews
28 hotel reviews
56 helpful votes 56 helpful votes
5 of 5 stars Reviewed August 4, 2013 via mobile

We have stayed here every summer, for about the past 15 years, and wouldn't go anywhere else. The rooms are large, impeccably clean and have nice decks. And, yes, Loren and Annie have rules, but that's one reason we stay there. It's just very nice and quiet, and you won't find nicer rooms and better value.

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Pewaukee, Wisconsin
Senior Reviewer
8 reviews 8 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed October 8, 2012

I could not have been more pleased with our stay at this inn! From contacting Loren about the room and details to the incredibly clean rooms and grounds. Loren and his wife were very very nice and happy to help you in any way. A lot of charm to this old school house turned inn. Yes the floors are squeaky,... More 

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Milwaukee, Wisconsin
Senior Reviewer
10 reviews 10 reviews
3 helpful votes 3 helpful votes
5 of 5 stars Reviewed October 7, 2012

I just arrived home from my first stay here. I was slightly hesitant upon my arrival after reading the reviews. I will say that as a WEEKLY business traveler for 5 years I have never seen a cleaner room! We stayed in the Homestead Suite. It was super quiet at night. Baileys Harbor is on the quieter side of the... More 

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Mokena, Illinois
Contributor
18 reviews 18 reviews
8 hotel reviews
6 helpful votes 6 helpful votes
3 of 5 stars Reviewed September 5, 2012

Only complaints were the horribly squeaky floors and the worn out bed. You roll to the middle of the bed. Also the bed is advertised as "Queen size". It is a full size bed, not a queen size. The room (Upper Deck) was nicely decorated and comfortably furnished. We weren't given any "rules" and the owners seemed fine. One telling... More 

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Milwaukee, Wisconsin
1 review
2 helpful votes 2 helpful votes
1 of 5 stars Reviewed July 21, 2012

We found Orphan Annie's at Bailey's Harbor and wanted to reserve for mid July 2013 for a dance festival in Door County. We talked to the innkeepers on Sunday, July 15, 2012 and reserved a room and wrote a check for 1/2 of the amount. We were given the "rules" of no more that 2 guests for only 1 hour... More 

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Chicago
Top Contributor
131 reviews 131 reviews
45 hotel reviews
113 helpful votes 113 helpful votes
5 of 5 stars Reviewed July 14, 2012

If you don't need a lake view, this is a lovely place to stay. It's one block out of the center of town, so you can walk to the lake in minutes. The old converted school house is on a park and very quiet. The rooms are large and comforable, each with porches. They don't serve breakfast, but they have... More 

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Madison, Wisconsin
1 review
5 helpful votes 5 helpful votes
1 of 5 stars Reviewed July 10, 2012

My warning system went on alert immediately as there were notes with rules pasted all over the room, including cleaning the shower stall every day. Some friends of ours live in the area and wanted to see the room. Oh my lord, you think we were having a bachelor party the way Loren reacted. We were lectured and scolded as... More 

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Fairfield Glade, Tennessee
Top Contributor
63 reviews 63 reviews
12 hotel reviews
13 helpful votes 13 helpful votes
5 of 5 stars Reviewed November 18, 2011

We recently stayed here for the second time, and confirmed that it's indeed a wonderful choice. A very unique place, my wife and I stayed in the Library room (was actually the library when the building was a school) which is more like a suite. It has a small kitchen area, walk-in closet and lots of space. It's decorated with... More 

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